Highland Square Vacation Packages for 2026

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Highland Square Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Streetsboro, OH

Motel 6 Streetsboro, OH

2 out of 5
Price was $303, price is now $259 per person
$259
per person
May 21 - May 25
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Akron (CAK)
Book a stay at this business-friendly motel in Streetsboro. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions ZipCity and Boulder Creek Golf Club are located nearby.

DoubleTree by Hilton Akron Fairlawn

DoubleTree by Hilton Akron Fairlawn

3 out of 5
Save 100% on your flight
Price was $704, price is now $513 per person
$513
per person
May 21 - May 25
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Akron (CAK)
Book a stay at this business-friendly hotel in Akron. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Blossom Music Center and Summit Mall are located nearby.

Courtyard Akron Downtown

Courtyard Akron Downtown

3 out of 5
Elizabeth Park Valley
Price was $617, price is now $467 per person
$467
per person
May 21 - May 25
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Akron (CAK)
Book a stay at this business-friendly hotel in Akron. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Akron Art Museum and The Glendale Steps are located nearby.

Holiday Inn Express Akron NW - Fairlawn by IHG

Holiday Inn Express Akron NW - Fairlawn by IHG

2.5 out of 5
Price was $511, price is now $396 per person
$396
per person
May 21 - May 25
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Akron (CAK)
Book a stay at this business-friendly hotel in Akron. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Blossom Music Center and AMF Riviera Lanes are located nearby.

Sheraton Suites Akron Cuyahoga Falls

Sheraton Suites Akron Cuyahoga Falls

3.5 out of 5
Price was $689, price is now $565 per person
$565
per person
May 21 - May 25
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Akron (CAK)
Book a stay at this business-friendly hotel in Cuyahoga Falls. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Blossom Music Center and Cuyahoga Falls Riverfront Center are located nearby.

Staybridge Suites Akron-Stow-Cuyahoga Falls by IHG

Staybridge Suites Akron-Stow-Cuyahoga Falls by IHG

3 out of 5
Price was $563, price is now $468 per person
$468
per person
May 21 - May 25
found 19 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Akron (CAK)
Book a stay at this business-friendly hotel in Stow. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Blossom Music Center and Cinemark Cuyahoga Falls and XD are located nearby.

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Top Hotel Deals

Berrodin Bed & Breakfast

Berrodin Bed & Breakfast

3 out of 5
814 Bloomfield Ave Akron OH
0.61 km from Highland Square
Stay at this B&B in Akron. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Highland Theater and Dr. Bob's Home are located nearby.
Comfort Inn & Suites Cuyahoga Falls - Akron

Comfort Inn & Suites Cuyahoga Falls - Akron

3 out of 5
1420 Main St Cuyahoga Falls OH
5.98 km from Highland Square
Book a stay at this business-friendly hotel in Cuyahoga Falls. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hyatt Place Canton

Hyatt Place Canton

3 out of 5
5421 Whipple Ave NW North Canton OH
28.56 km from Highland Square
Book a stay at this business-friendly hotel in North Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
La Quinta Inn & Suites by Wyndham Cleveland Macedonia

La Quinta Inn & Suites by Wyndham Cleveland Macedonia

3 out of 5
268 East Highland Rd Macedonia OH
22.36 km from Highland Square
Book a stay at this business-friendly hotel in Macedonia. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Econo Lodge Cleveland Southeast - Kent

Econo Lodge Cleveland Southeast - Kent

2 out of 5
9789 State Route 14 Streetsboro OH
22.77 km from Highland Square
Stay at this hotel in Streetsboro. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Best Western Plus North Canton Inn & Suites

Best Western Plus North Canton Inn & Suites

2.5 out of 5
6889 Sunset Strip Avenue NW North Canton OH
26.08 km from Highland Square
Book a stay at this business-friendly hotel in North Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Hampton Inn Medina

Hampton Inn Medina

2.5 out of 5
3073 Eastpointe Dr Medina OH
21.25 km from Highland Square
Book a stay at this business-friendly hotel in Medina. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Cambria Hotel Akron - Canton Airport

Cambria Hotel Akron - Canton Airport

3 out of 5
1787 Thorn Drive Uniontown OH
16.91 km from Highland Square
Book a stay at this business-friendly hotel in Uniontown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Embassy Suites by Hilton Akron Canton Airport

Embassy Suites by Hilton Akron Canton Airport

3.5 out of 5
7883 Freedom Avenue, N.W. North Canton OH
24.76 km from Highland Square
Book a stay at this business-friendly hotel in North Canton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
The Aurora Inn

The Aurora Inn

3 out of 5
30 Shawnee Trail Aurora OH
29.54 km from Highland Square
Book a stay at this business-friendly hotel in Aurora. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular ...
Hampton Inn Akron-South

Hampton Inn Akron-South

2.5 out of 5
880 Arlington Ridge East Akron OH
13.59 km from Highland Square
Stay at this hotel in Akron. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
Kent State University Hotel and Conference Center

Kent State University Hotel and Conference Center

3.5 out of 5
215 S. Depeyster Street Kent OH
17.08 km from Highland Square
Book a stay at this business-friendly hotel in Kent. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean ...
Holiday Inn Canton (Belden Village) by IHG

Holiday Inn Canton (Belden Village) by IHG

3.5 out of 5
4520 Everhard Rd NW Canton OH
28.52 km from Highland Square
Book a stay at this business-friendly hotel in Canton. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Pro Football Hall of Fame ...
Motel 6 Streetsboro, OH

Motel 6 Streetsboro, OH

2 out of 5
9371 State Route 14 Streetsboro OH
22.75 km from Highland Square
Book a stay at this business-friendly motel in Streetsboro. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and ...
Comfort Suites Brunswick Town Center

Comfort Suites Brunswick Town Center

2.5 out of 5
1464 Town Center Boulevard Brunswick OH
26.6 km from Highland Square
Book a stay at this business-friendly hotel in Brunswick. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, May 5 - Thu, May 7
LGA
LaGuardia
CLE
Hopkins Intl.
$66 Roundtrip, found 1 day ago
$66
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, May 5 from LaGuardia to Hopkins Intl., returning Thu, May 7, priced at $66 found 1 day ago
JetBlue Airways
Sun, May 10 - Sun, May 17
JFK
John F. Kennedy Intl.
CLE
Hopkins Intl.
$157 Roundtrip, found 1 day ago
$157
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sun, May 10 from John F. Kennedy Intl. to Hopkins Intl., returning Sun, May 17, priced at $157 found 1 day ago
Southwest Airlines
Thu, Apr 9 - Sun, Apr 12
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Thu, Apr 9 from Hartsfield-Jackson Atlanta Intl. to Hopkins Intl., returning Sun, Apr 12, priced at $159 found 3 days ago
Delta
Thu, Apr 9 - Sun, Apr 12
ATL
Hartsfield-Jackson Atlanta Intl.
CLE
Hopkins Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Apr 9 from Hartsfield-Jackson Atlanta Intl. to Hopkins Intl., returning Sun, Apr 12, priced at $159 found 3 days ago
Spirit Airlines
Tue, Mar 24 - Sun, Mar 29
FLL
Fort Lauderdale - Hollywood Intl.
CLE
Hopkins Intl.
$170 Roundtrip, found 3 days ago
$170
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Tue, Mar 24 from Fort Lauderdale - Hollywood Intl. to Hopkins Intl., returning Sun, Mar 29, priced at $170 found 3 days ago